On the occasion of his fiftieth anniversary, Seventh Avenue's éminence grise talks with Daphne Merkin about his vision of retro-debutante elegance—which has never looked more modern than now

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"I hate pretty," Oscar de la Renta, whose way with a certain kind of exquisite party frock is second to none, is saying in his charmingly accented English. "It's a very empty word. It gives a bad name to beauty." The 81-year-old designer breaks into song—"I Feel Pretty" from West Side Story—to illustrate his point or, perhaps, send it up. One thing this urbane, impeccably dressed man with a permanent twinkle in his eye doesn't do, I quickly discover upon visiting him in his white-on-white offices on West 42nd Street, is take himself—or the world of fashion, for that matter—too seriously. He mentions coming upon a bunch of his old designs in Barneys' vintage department and confesses to finding some of them "hideous." Which isn't to say that he doesn't pay meticulous attention to how the clothes drape on his models or who his customers are, just that it is all part of the larger picture show.

When I arrive at 2:30 on a weekday afternoon in late September, de la Renta is sitting at a round table near the window, finishing up a delicious-looking repast. There is a box of figs as well as bottles of olive oil and balsamic vinegar on the table, and the mozzarella and tomatoes on his plate glisten with a farmer's-market freshness. "I never go out for lunch," he announces, and offers me a drink made of turmeric. Earlier in the day, de la Renta tells me, he attended a global initiative on behalf of elephants, which is a pet cause of his wife, socialite and philanthropist Annette; the Clintons and Kissingers were among those attending. Ever since he arrived on these shores half a century ago, from his native Dominican Republic, having stopped along the way to sketch for Balenciaga and work for Lanvin, the designer has straddled the worlds of high fashion and high society with great ease. Already in 1967, he was described by a journalist as "a comet on the American style scene," someone who made clothes for the wives and daughters of rich and powerful men but also moved among the group known as The Beautiful People himself. He sprinkles fabled names—Nan Kempner, Gloria Guinness, and Babe Paley—into the conversation, not to impress (he strikes me as the least snobby of men), but because they come naturally to him. His memories seem vivid but not airbrushed: "Not even her husband saw Babe without makeup," he says, chuckling.

The remarkable thing about de la Renta—which explains both his longevity and his relevance to the current red carpet—is that, despite his familiarity with the chic women Truman Capote referred to as his "Swans," the pocket square he wears in his pin-striped suit, and his wonderfully old-world manners, he is completely of the moment. "Fashion," he says, "is about the present and the immediate future. I think in terms of now." He is not, to be sure, an advocate of futuristic fantasy: "Cardin and his space clothes," he asks almost apologetically, "where are they now?" But just as importantly—and more impressively, given his own éminence grise status—he refuses to indulge in nostalgia. Not for him the backward glance at a vanished era of rule-bound fashion or the bemoaning of the disappearance of a certain kind of formal "ladies who lunch" dressing. "I have seen the emergence of a different customer, a different woman," he says, a hint of pride in his voice. "I love to think that I am a much better designer today because I have a better understanding of the customer. She is someone who will choose the red dress over the pink, even if her husband prefers the pink." He seems to delight in the new order of things, right down to the fact that he places women who care about brands on a "list of endangered species," adding: "There is no loyalty among consumers today. How she dresses is a reflection of who she is."

Among the strategies de la Renta has employed to keep himself au courant is keeping younger eyes around him. These include his stepdaughter, Eliza Bolen, who oversees licensing, and her husband, Alex, who heads the company, as well as stylist Alex White and director of communications Erika Bearman—the latter better known as the Twitter phenomenon OscarPRGirl. One wouldn't expect a luxury fashion house steeped in tradition to excel at social media—the designer himself is partial to phone calls and letters—but this is exactly what has transpired, due largely to Bearman's chatty and likable presence. Her Twitter feed, which has been described as a "Carrie-Bradshaw-esque life-stream," includes insider details about the house and select personal tidbits. It doesn't hurt that Bearman is very photogenic and wears de la Renta's designs with a casualness, a kind of benign irony, that undercuts their festive glamour—almost as if she were a debutante posing as a working woman.

Given Galliano's unerring instinct for style and currentness, it's perhaps not so surprising that de la Renta extended an olive branch to the ostracized younger designer. "He's a nice guy," de la Renta says. "I've known him 30 years. I do believe people deserve a second chance. He feels so repentant." The odd truth is that there is more in common between the Sultan of Suave, as he's been called, and Galliano than not. Both have a sure understanding of cut, an appreciation of fabric, and the sense to know that to stay vibrant couture must follow the consumer's lead: "Elegance is an old word," de la Renta says. "A lot of anonymous girls walking along the street have a style of their own."